Jeffery: Well like, we like to do we just like to jump right into things, Ash. So again, thank you very much for joining us today. Welcome to the supporters fund Ask An Angel. I’m your podcast host, which is Jeffery Potvin, and let’s welcome, Ash, to our podcast today. So welcome Ash! Thank you for joining us.

Ash: Thank you very much for having me.

Jeffery: And I’ve been pretty excited because, I will tell you that you have the longest Linkedin profile that I have ever read, which is amazing.

Ash: Wow.

Jeffery: Yeah.

Ash: Wow, okay.

Jeffery: A lot of content.

Ash: Okay.

Jeffery: Secondly, you have a lot of great audio and video, a lot of material on yourself. So it’s been delightful being able to go through and learn so much about you. So I’m glad for that, and your book is fantastic! So..

Ash: Thank you very much! It’s very nice of you to say.

Jeffery: Big fan. I will write a review for the book, eventually.

Ash: Yes, please do that. Amazon reviews are the most influential, are some of the most valuable currency in the world. Especially from (inaudible 1:03).

Jeffery: I could imagine, I could imagine. But it honestly, it’s a great read.

Ash: Thank you.

Jeffery: I will- but just to start off, just to kind of jump us right into it. Before we dive into all of this amazing data on yourself and the things that you’re doing, I’d like to see if we could share a little bit about your past, your background, a little bit about where you are today, and then one thing about you that nobody would know.

Ash: So I have been very interested in pulling apart computers and pulling apart companies. Two very different things for a very long time and for very different reasons. You know, interested in pulling apart computers because I just got curious. You know, I grew up at the time where you know computers started being in people’s homes and so, I had one at home and used it for more and more things, and found little ways to make money by helping older people with computers when I was much younger. And that was all very fun so I just wanted to learn more and more. I was interested in pulling apart companies because my, and this gets the one thing that people probably don’t almost certainly don’t know about me is that, all of my family are entrepreneurs. My mom, my dad, my brother, and all of my grandparents. All started their own businesses separately. They also work together on some things but they all separately started their own businesses, and so I just sort of grew up thinking, ‘well that’s just what you do’. And so, you have to understand how to do that and you know, the conversations at dinner in the evening were about all the things involved in starting companies. And so I was interested in learning what makes a good company and one way to do that, of course, is trying, which I did, and started some companies. Another way you do that is by reading, which I did, and you read books but another is by investing in companies. So I started doing that pretty early on. Anyway, fast forward, this has led to various things, you know, one working as an investor across different asset classes, public equities, growth investing, and then for the majority of my career by far venture capital, and then also starting companies. I started a company that managed data for big hospitality companies like the biggest hotel company in the world IHG, the biggest airline in the world, United or biggest allied loyalty program in the world, we built software for them. I- we sold that company. I helped start the biggest fundraising platform in the world, Angellist. So when I got to Angelist, there were just five engineers, and the founders, and the designer, and I put together the first deals that happened through Angellist so the syndicate platform and everything else and that now sort of manages billions of dollars. And then my partner, Mark, started and then I joined a year in, and we launched together the first venture capital fund focus on artificial intelligence and that has led to working with a whole bunch of pioneering artificial intelligence companies, like Kaggle, Clear Bit, Lilt, and Vania Domino, etcDomo. And we have worked with lots of those companies and accumulated a bit of knowledge about how to run such AI first companies, and put that into a book, which you kindly mentioned called, “The AI First Company.”

Jeffery: I love it and before we dive in, one thing about you. I know you mentioned there’s one but maybe there’s some other things that you can share. But what’s one thing about you that we wouldn’t know?

Ash: Oh that’s what I shared which is all of my family are entrepreneurs. Every single one of them.

Jeffery: Oh okay, yes. I was always thinking about something else. That’s brilliant.

Ash: Another thing is, I have, it’s an insight into my personality. I have 10 different ways to make coffee in my kitchen. So you know, I’m a highly caffeinated individual. There you go.

Jeffery: That’s an interesting one. I’ve never heard that analogy. That’s brilliant. So to kind of, before we jump into the book and all these other things, I kind of want to go back to some of your past and being in the data company, working in banks, having a family of entrepreneurs, how much of that lifestyle really shaped who you are today? Do you believe that a lot of that early stage learning really shaped how you were gonna invest the types of companies you went after, the areas you got into? And was it part of that growth part that you needed to be in the bank, you needed to learn the process, you needed to learn about how data worked, before you got into entrepreneurship, before you got into seeing and learning what your family was all about? How do all those things kind of help deliver to where you are today? Do you work off those past experiences?

Ash: Well, I don’t mean to sound facetious but, of course, I do. Like, and to be philosophical for a moment, how else do you learn? That’s a contentious statement but I think people underrate their experiences, their own experience as informative of what they should do next, and sort of overrate the experience of others. That’s certainly a belief I have and therefore, I certainly do weight my own experience, and use it to inform what I do next but in a very like, straightforward way. You know, I just tried things and when I was good enough at them to get the next opportunity, I took the next opportunity, and I just kept trying and trying. So yeah absolutely, you know, I tried starting a company and it sort of worked out. And I tried working on another company, and it sort of worked out and so on and so forth. And you know, you just keep you just keep going. When the ‘going’s’ good, you keep going, and when it gets hard you go home and you think about it, you try something else.

Jeffery: And I’m guessing, when you tried something else so you kind of worked on that next thing, was it more of a learning approach for you? It was: ‘This interests me. I’m gonna dive in and learn about it because I know I can and I should.’ And that comes back from that sitting around the dinner table and talking to all of the entrepreneurial family you have because they were trying things, they were trying to solve problems, and you learn from that so kind of that mentality carries back that, “Hey, you know what, I can try and solve any problem. And you know what, today I’m going to tackle this one. I find the challenge is there and I want to work on this.”

Ash: Yeah sure. I guess, I’m just like quite pragmatic and what’s more of a doing approach for me in that, often I just take on the next task because I want to just keep moving forward, and I firstly, there’s not much else you can do besides move forward and learn that way. And two, I learn, sort of very kinesthetically, by doing something. Not auditorily or otherwise. So you know, that’s certainly something that’s informed me over the years. Also, that’s a belief I’ve come to have over the years or something I’ve learned about myself. So no not necessarily. All of that said, like, yeah I’m super curious. I’m always reading. Curiosity’s sort of my driving motivation a lot of the time. Nothing more, nothing less.

Jeffery: I like it and I’m kind of intrigued by this whole family of entrepreneurs because I think a lot of, maybe in the generation that we’re in, there wasn’t as many entrepreneurial families as there certainly is today and there’ll be a whole generation in the next 20 years of everybody will be an entrepreneur. It seems to be shifting a lot into that space. So as myself growing up, I looked at entrepreneurship because I looked at it as: ‘How do I progress something forward? How do I make a dollar for myself? I don’t want to lean on anybody else. I don’t want to go to somewhere else to get it. I want to figure out how I can get it.’ So, but the rest of my family wasn’t like that. So they all worked in business, and etc. How much of that environment really makes a difference? Because I was on a call yesterday with a venture fund and they focused just on immigration, immigrant founders, and the reason they do it is, they said because they have a hustle that nobody else has. They’re there to make it happen. They’re going to make it work. And I love that because I can understand that they’re going somewhere new and they got to fight hard to make it work. So being in a family that had that same mentality, did you see that that really helped you move quicker in the landscape and de-risk it? Because you kind of could see through all of the family that, this is what Albert did, and this is what she did, and he did. So there was always that learning curve that you could push yourself forward quicker and it made a real big difference in your entrepreneurship.

Ash: Yeah, that’s one theory, for sure. You know, for me it was more about the absence of fear rather than the presence of motivation. The presence of motivation was certainly there like when you come from a family that’s left a war-torn country and arrives in the country that has opportunity and did well for themselves, you sort of feel very grateful for that. You feel like there’s an obligation to keep solidifying things and to make good of the opportunities being presented to you because it wasn’t that easy to get there and to generate those opportunities, so there’s certainly a presence of motivation but it’s more the absence of fear. Like once you see that okay you know, people can start their own business and feed two kids, my brother and I. You know, we always have food on the table. So it’s like, “Well, how bad can it be? Like starting a business?” A lot of people are really afraid of studying business because they’re afraid of like just not being able to provide for basic needs in their family and I haven’t had that fear for a long time and it’s because I saw it was possible.

Jeffery: I like that and wholeheartedly agree, that once you start to tackle through this fear, which is I have a regular paycheck, it comes in at this time, I pay the bills, I go forward. Once you break down those barriers or at least put yourself into a space where those no longer happen, and you’re not getting that continuous paycheck and getting that continued or then it goes on to that fight you have to kind of move yourself forward, and I think a lot of people have that fear of having to fight.

Ash: They do. Yeah.

Jeffery: That’s what kind of becomes almost crippling to that person because they can’t move into that entrepreneurial space because they’re used to having that support mechanism.

Ash: Yeah. I think so.

Jeffery: So it’s great that you were able to see that and learn through that as well.

Ash: I think so. I think that’s a big deal for people.

Jeffery: So when you started to go into your first business, you launched it, actually you have quite a few businesses that you went into and started, built, sold. Is there, maybe a couple of points that you could take from there and say, “You know, here’s the things that I learned as a founder,” and because I’m really interested now as we shift into the investor side, a lot of the times when you’re a founder, you either continue to keep founding businesses. You don’t really get into the investment side.

Ash: Yeah.

Jeffery: You kind of took the total shift and said, “You know what, I’m going to go into the investing side because I have a really strong ability for this.” So what kind of things did you learn from being a startup and how much of that transfer into being a VC?

Ash: So I think what you learn, functionally, like how to sell, how to manage the build of a product, or that sort of stuff, quickly becomes irrelevant. Also, you know, unless you really do it for 20 years in a very functionally specific way, you’re not really in a world expert at it. I think a lot of that functional knowledge is pretty limited. I think a lot of the domain expertise, you know, working in the hospitality industry, travel industry, whatever, that fades really quickly. People change, people leave their jobs, the industry change, the dynamics change, obviously they have in the travel industry over the last year. I frankly think a lot of that is like completely overrated, in terms of the transferability to the investing world. What is somewhat underrated is just the empathy of being in a position where you’re trying to start something from nothing. Where on any given day, big companies who you want to sell to don’t care. They just don’t care. They don’t need to do anything. They’re incumbent. They don’t need to buy you a cool new technology product where investors just don’t care. They don’t need to make any investments. They don’t need to make. If they do make, they don’t need to make that money. They just don’t need to deploy capital. So you’ve got to convince them. Employees, potential employees, candidates at big companies who have nice jobs, they don’t care about your startup. You have to really convince them and that’s a really tough position to be in every single day, where you’re trying to create something from nothing and you can try to- you’re trying to convince people that have absolutely no incentive to care about your startup that there is a reason they should care about your startup. Whether it’s to fund it, to buy your product, or to join you in the journey. And knowing what that feels like, I think is really important as an investor because you can make that feeling worse as an investor or you can make it better by how you sort of talk through things and having an appreciation of it, and that’s one thing. And then also just the ability to operate under such massive uncertainty. I think that’s really important to appreciate for somewhat obvious reasons, you know. It’s not possible to know everything at any given time and as an investor, if you don’t appreciate that you’re going to just be annoying someone for answers that they don’t have. And that’s just going to frustrate everyone, so I think that’s something that transfers really well over to being an investor. And the other thing besides just sort of the struggle of getting people to care, and dealing with uncertainty, is also just the prioritization function where I found it, it’s like much more existential than marginal and that is, you know as a founder, you really have one priority at any given time and it’s usually to address the thing that no one else can address, except the founder, and that if not addressed will mean the company’s dead. And just knowing that that’s what a founder’s function is, to address and mitigate existential risks in a business, is really important because again, otherwise, you’re bugging them as an investor to do a whole bunch of things that they’re just not going to do or they shouldn’t do, and if you bug them enough maybe they will start doing those things and then all of a sudden the company dies because they’re not addressing the right thing. So anyway, I think those three things transfer well.

Jeffery: Which is interesting and especially, on the last one where you’re kind of working through the risk side of things and the roller coaster ride of your business, that obviously is a good thing from an investor’s standpoint to be able to know that this is what a startup would be going through, and that at any point, they could be at the top of their game, at the bottom of their game, that they’re going to need some sort of support. But it’s also understanding that and I like what you said about, no one cares. You have to create the care inside of that customer and you have to understand what the problem is, which means that and I’m going to just kind of peel back and say this is what you’re looking for, but is it a focus and you’re making sure that, that founder and that company that startup has a real genuine deep focus on that customer? So that they are working inside that problem, they’re working inside that customer, and they’re really trying to gauge that, because if they don’t, the success is going to go out the door. The company’s not going to say, “You know what, I get what you’re doing but I don’t.” So-

Ash: I agree. That’s really important.

Jeffery: – a big chunk of it.

Ash: Yeah, it’s hugely important.

Jeffery: So transferring these skills into a VC side and you kind of mentioned it, that you’ve got this knowledge of working in travel industry, how does that make you a good investor then? Or you work as this and now this gets you into this one? So what kind of skills do you need to build up on the investor side? And this though are those skills again, did you learn them? You just didn’t fully utilize them as a startup but they’re there. So as you kind of build up financial documents, you build up the next five-year run rates, you’re building up all of these things, is that kind of helping you get into that VC market? Or that learning market for investing? –

Ash: Oh.

Jeffery: Have you gone through it?

Ash: Yeah, sorry. I guess there’s probably just a bit of context missing here, which is I was an investor before I was a founder, and then went back to investing, and then went back to sort of quasi-founding. So I started as an investor. Investing was always my craft. So I think that’s my answer to this question is not very useful because I always knew I wanted to be an investor and I started learning the skills necessary to be invested at a very young age. I started learning accounting, and finance, and law, and valuation, and then we get more and more specific: technical analysis, personality assessment, all those sorts of things that are really important and that are very distinct skills like, there’s lots of literature and courses, university courses, and otherwise that you need to take, and certifications you need to get and whatever, and I started getting them, you know, very very long time ago. So I did that. You know, I think if you are someone that’s trying to move from the world of starting companies into investing, you need to be ready for 10 years of learning. You need to very deliberately approach that learning and if you just think you’re going to learn it on the job, like frankly you’re taking a responsible approach because that means you’re gonna lose a lot of money that you don’t need to lose. So I think it needs to be a very deliberate choice and very backed up by very deliberate effort to learn very specific skills.

Jeffery: That’s great advice, and interesting, learning. I was talking to, actually he was a Canadian living in Australia right now. He’s an investor and he said that when he went to become a VC, they told him, “If you want to be a VC you need one x.. you need to have an exit, and you need an MBA.” So he went and got his MBA, and he exited one of his companies. So I guess there is some protocols that fit into this stage of what type of learning do you need in order to go from an entrepreneur into an investor.

Ash: Yeah, so yeah. Lots of different firms have lots of different approaches to figuring out what they want to see in someone before they start working with them, and I think there are lots of ways that you can figure out if someone might be well-suited. But at the end of the day, it’s a long path and everyone has to be ready for that. Takes a long time to learn all the constituent skills of being a great investor.

Jeffery: I will agree with that. There are lots of bumps in that road. It all starts with the main one that we all fight with, which is your most expense, which is resource, and it happens to be the same thing that controls and manages a startup. And they’re the, I think in any investment you make they always seem to be the hardest team or hardest part that you’re investing in to know that that’s going to be something that’s going to be able to grow and build inside of a business even though it’s the wild card that changes quite frequently.

Ash: Yeah. It is, yeah.

Jeffery: So as you’ve kind of gone through this journey, you’re investing, you’re working in your own startups, you’re moving through this amazing journey of all these things that you’ve done, great investments, you decide to write a book. And the book isn’t about venture capital or investing in venture capital, I guess a little bit of it is of course, but you dive right into this whole new space. Again, this isn’t a new space but it has been mediaized as being new in the last, I would say probably the last five years it’s really skyrocketed, and everybody, and their grandmother needs to learn how to develop an AI because it is one of the fastest growing skill sets outside of data. Maybe you can walk us through a little bit about what got you interested to write a book and, of course, on the side of doing it in AI.

Ash: Sure. Well, the second part of that’s easy. I’ve been solely focused on backing and working with air force companies for eight years now, and I’ve started an air force company or a data company, which is a precursor. I guess to an air force company to you for two years, it’s been a decade of work. So you know, this is what I know, this is what I do every day, and this is the body of knowledge, I’ve accumulated a body of knowledge around this space. This is the space around which I’ve accumulated knowledge that, you know, isn’t really well propagated, and so that gets to the first part of your question, which is why write this book. I think it’s just a moral good to share knowledge and to add knowledge into the world because people can leverage that really easily to do all sorts of great things in their life, and it just sort of became obvious to me that I had a little tiny bit of knowledge that other people didn’t have and it was time to share it. There’s a huge amount of work to share it, to write a book, and whatever else but I think it was the right thing to do, morally. That so, that was a huge motivation. And secondly, you know, it just makes conversations a lot easier every day. You know, someone comes to you with a question and you’re able to point them to an answer they can go away they can read it, and then they can come back to you with a really really good deep question quite soon after that, rather than having to sort of have them ask a question, you fumble through an answer, then they have to clarify it, and so on and so forth. It’s just good to be able to give my most clear possible answer. I’m not saying all of my answers in the book are very clear. All my points in the book are crystal clear but those clear as I can possibly articulate them at this point in time, and be able to give that to someone, have them work with it and then go from there, and then get to that deeper level of conversation really quickly. So I’m able to, one, say that I thought it was just a good thing to do to share knowledge. Two, have deeper and better conversations with founders and people at big companies with other investors, with all sorts of people. And three, you know, I’m able to sort of now take that as my knowledge at this point in time and then really work with it. You know, it’s one thing to work with an idea in your head and sort of come back to it, and maybe think about it incidentally while you’re going for a walk. It’s another thing to put everything on paper at a point in time and then a year later go, “All right, it’s time to write a second edition.” What do, what has actually changed? What do I know that’s actually a bit different to what I knew a year ago? So it’s just good to have those junctures.

Jeffery: So when you were going through your original analysis, and going through the eight years before you wrote the book, and went through all of the contexts and learnings, and said “You know, this is where I’m going to start the book, and how it’s going to work through.” Taking all those learnings and what you’ve put into it, I’m curious, how long does it take to write a book? Is this something that you started eight years ago, and just started piecing it together until you got to this final stage and then kind of submitted it and went through iterations? And then second, when you kind of get this into the right spot, who do you have to put it in front of to kind of pack it for you? So that, like you said, you’ve got all this knowledge you want to share, so do you have to get some, I don’t know, science, acumen behind it and have like 10 of these amazing people that have to read your book in order to approve it? How does that whole scenario work? Because I think what I read in the book is that, there’s a lot of amazing learning but there’s also a lot of things that and we’ll get into what how you structure lean AI. I think a lot of businesses should read this because they could actually get their s stuff together because I think a lot of them are taking the wrong approach on how to implement AI, and I think what you put together, I literally will be sending this out to business people and saying, “Man, you guys need to learn about AI because you’re doing it all backwards.” So-

Ash: Yeah

Jeffery: So, I’m just curious, is that how that approval process worked for you? Or do you not care and you’re saying, “You know what, I’ve been doing this so long that this is how it’s got to be done. Just follow this structure and you’ll get where you need to be.”

Ash: Yeah. So it wasn’t ‘I don’t care’, it’s just that, you know, this is a set of original concepts that I came up with and so they are as long as they’re internally consistent. They’re correct and so I just tried to make them as consistent as possible internally. And therefore, they’re correct and usable. Secondly, you know, this is what I do all day long so it’s sort of hard to be too wrong about it for 10 years, and then you know, thirdly, I did have editors to just sort of help me with things on on the margins but those people quite helpfully didn’t have any background in my space at all. The editors that work at publishing companies that haven’t worked in AI before. So they were able to sort of just ask good questions. “Well, what’s this? What’s this?” Every single term I use, what does that mean? That’s you know, also what led to that very big glossary at the end of the book, which I think is really helpful because again, it makes the book useful on a standalone basis. You don’t have to go and look anything up to understand the content of the book. You have to read another book to understand this book. It’s all there. So that’s what that approval process looks like. To the first part of your question, around how long does it take to write a book. You know, because I’ve spent so much time in this area, it really didn’t take me that long. I wrote, and this is a little bit poetic in a way but it’s it’s totally true, I wrote a third of the book in three days, and I wrote the next two-thirds of the book in three months, and then I rewrote the entire book in another three months, essentially. So I just got a lot of stuff out in a couple of days, then I sat down and forced myself to write 500 words a day, every single day. Sometimes it was good, sometimes it wasn’t so good, sometimes it took me 20 minutes, sometimes it took me 4 hours to write 500 words, and I did that for three months. And then I came back to it a while later and, you know, based on a bit of feedback here and there and based on some new ideas rewrote a lot of the book. Now, I was doing this all part-time outside of work. Outside of my day job as an investor, so you know keep in mind when I say three months, I mean three months like strictly part-time or strictly, you know, on at night time. So that that’s how long it took me to do it, and of course after that, I should say there’s a lot of work on illustrations, editing, dealing with various publishing requirements, and that sort of thing.

Jeffery: And when you said you rewrote the book, is this because you created a template and when you read through it, you just reorganized it? Or did you literally have to rewrite everything in a simpler context? Or how did you look at that?

Ash: All of the above and more. It was structural. It was also, you know, a laboratory. There were certain points that needed more explanation, elaboration, or where that would be it, would have been useful or was useful, and then it was also conceptual in that. You know, over time, I’ve sort of realized, “Oh, this is the core concept behind everything I’m saying. So why don’t I just explain that up front?” That is a data learning effect, and then I can reference it throughout the book.

Jeffery: I love that because to me that just goes back to the topic we were on, which was focus is that, as you started to read through, you started to pull out that main focus of the book or the main problem you were solving, just like a startup would, and then restructured it around that problem so that the reader would be able to understand from beginning to end what you were really trying to solve throughout the book.

Ash: Yeah, exactly.

Jeffery: For me, it was so much around process, obviously, on the data side, which I love data I love the whole concept everything around it. But I just like that there was a lot of input on how to do these things, how to organize yourself, how to organize your teams, and I liked, maybe you can share a little bit about it, but certainly on the the lean AI side, I think was, and again, I think when you run a business, your brain doesn’t go to how do you create a nice little simple process. Maybe you do later on after you’ve been doing it long enough. But I think a lot of people just jump into something just to say they’re in there doing it. They haven’t really organized it in any way or any fashion. So they’ve probably scattered, they’ve got in their at least in their AI side, they haven’t organized it properly. So you’ve got teams doing all these different things but they’re not really connecting properly, and I think just the process that you created around the lean AI model. I just thought it was very easy and it was very easy to understand. So maybe and I think there was five great points but maybe you can share a few of those for the the listeners. I think it would be great to learn that.

Ash: Yeah, lean AI is all about how do you create a way to figure out if you can make a prediction that’s valuable. Just using one data set, one way to model the problem, with one output, like one report, one table, one chart, one page, or whatever, and run it on one system with one person. That’s what lean AI is all about. It’s about breaking down the hypothesis you have, around what sort of prediction you can make so that you can just get it done, and then figure out, ‘Okay, if we want to make this prediction better, where do we allocate capital?’ do we spend money on data? Do we spend money on computing to run the model more times? Do we spend money on consulting to figure out different ways to model this? With like a data science consultant? Well, what else do we do? Or do we spend money on like, building an interface so people can consume the prediction better, and therefore, make it more usable like the accuracy is actually up there, but the understandability is not? So we have to build an interface, so we just spend money on software development. Do we spend money on that?’ So that’s what lean air is all about, sorry, lean AI is all about, which is to ask a series of questions so that you can narrow down the problem in that way.

Jeffery: And I liked that you did narrow it down, and you’re like using one algorithm. Don’t use 40, use one, and figure it out, keep cleaning it up, keep changing it, get it to the point where you’re going to get the right output. Get it to 96%, not 20%. Like build up the value so that everybody can understand what you’re trying to achieve by doing that, versus, doing too much, having too many algorithms, and too much data that doesn’t match up because you’re going to end up failing.

Ash: Yeah, exactly. That’s the goal.

Jeffery: I think it’s brilliant and, again, I don’t- I see it that a lot of people approach it in a different, which is get as much into the system as you can, we’ll clean it up after, and figure it out. But I think a lot of the time that data never gets cleaned up and then it becomes a very confused process, and then I think to you say in the book is that, then you’re not really solving a problem anymore. You’re not really working your way through to get the right data so that you have the right endpoint, so people aren’t going to see the value in what you’re trying to achieve.

Ash: Exactly, yeah. Exactly.

Jeffery: I like that. Now going forward, you created the book, you launched the book. I’m sure you’ve read the book a few times.

Ash: Once or twice. Oh that’s another statement.

Jeffery: Have you gone back and said, “You know what, I could polish this up. Chapter two could do some changes. I think I’ve learned a little bit different this way and I tried this with the team.” So has there been any, you mentioned that there’s version two or the next edition that comes out. Have you started to kind of gauge what that would look like or is it a total new-?

Ash: You know what, not yet because, you know, the thing was just published. You know it was only published at the time of we’re recording this. About seven weeks ago, something like that. So yeah it was only just published and, you know, we haven’t really had a chance as an editorial team to debrief on it but so far the feedback is such that you know most people are finding the ideas novel and applicable, and it’s more just a matter of them taking the time to apply them. And I think once people start doing that, and over the course of many applications and many rounds of feedback, we’ll learn a lot more. But you know, so far that’s what people have been all about.

Jeffery: I like it.

Ash: Like he’s just reading it, and applying it, and the feedback is good so far. Not- so nothing to drastically change. I will say, you know, there’s probably an opportunity to write a book with a lot of case studies. These gist that are just case studies of the concepts I wanted to keep that out of the core book because they get old really quickly and they tend to be cherry picked frankly. So I, you know, but maybe there’s a good book to be written or another supplement to be written with case studies. You know, there are other areas I’d like to explore. I’d like to explore more philosophical areas around like the epistemology of machine learning. Does it really add to our knowledge? And I’d like to explore areas around policy and regulation of these systems because you know these companies do generate a competitive advantage really quickly when they build these systems, and so I think more, sharing more knowledge about how that dynamic works, especially, with regulators would be really helpful.

Jeffery: I like that, and you, I think you always have to have a vision of something else you want to do and another problem you can solve, and then figure out how to layer one into two.

Ash: Exactly.

Jeffery: There was and, I’m pretty sure, I’m sure you’re probably familiar with blitz scaling.

Ash: Yeah.

Jeffery: There was the book that came out, I get maybe it was a year or two ago, great book. And now, there’s a lot, there’s a VC out of Silicon Valley, utilizing this book as their kind of their game play for what they’re doing on the venture firm side. You kind of see your book fitting into that same style that AI investors should read your book?

Ash: Sort of already been doing that but yeah. I mean, I’ve been doing that in a way and I’ll continue to do that. Like, you know, frankly if you want a lot more of the the lessons and the experience behind the book, I don’t know gotta work with me. So to get that and you know people that work with me on boards and whatever else, we very much have a good back and forth around a lot of the ideas in the book all the time. We’re applying them every day so yeah I’m already doing that and our founders are very much welcome to get in touch. If they’ve got an idea of how we could work together.

Jeffery: I love it. So you really are using the same model. I love that blitz scaling, using the book. When I talked to them, –

Ash: Yeah every single day.

Jeffery: – They were like, “You gotta read this book. This is what we do. This is how we do it. We’re changing the way you can grow your company and boom.” So I guess you guys can use that in the same conversation-

Ash: Me too.

Jeffery: – But I think it would fit really well. Oh, that’s awesome. Well we’re going to kind of keep shifting a little bit. I’ve got some great questions. I’m going to ask you in a short period of time, but then the next question is, what you’re doing right now? Can you give us a quick snapshot on kind of how the types of companies that you’re looking to invest at zetta?

Ash: Yep. Easy.

Jeffery: How are you guys are running the venture firm?

Ash: Yep.

Jeffery: Just a quick snapshot of how that looks.

Ash: Yeah, very easy. I am super focused on backing companies that are building tools and infrastructure for data scientists and machine learning engineers that are doing so in a way where, eventually, they’ll sell that product, those tools and that infrastructure. B2B, to other businesses, and are at the point where they’re just starting to sort of release those things, and need, you know, help in getting them to market. And then finally, at trying to sell that in sort of a bottom-up so to speak way. So trying to just get adoption more organically and then we’ll build the go to market function later on. The sales and marketing function later on, and then sorry, not finally, fifthly, doing that in a distributed fashion. So I’m mostly focused on companies that are, you know, building their team, and their business, and their company in distributed fashion, and I spend most of my time in Europe, in the UK. Where, you know, most people do things that way.

Jeffery: Okay, and that does that put you then more early stage, pre-seed, seed, because you are going in at that stage where they’re just starting to get out starting to learn a bit more about their customers?

Ash: Yeah. Look, I think what’s important is not what you call it but what it is, which is it’s backing people at the point where they want to really bring something to market. It might be tomorrow, it might be in a couple of months, but yeah they they’ve got something to bring to market. They just haven’t done that yet. And so, you know, I’ll help them figure out pricing, packaging. positioning, hiring, selling, marketing, and/or yeah, and much more. But that’s that’s where I start helping and you don’t have to have a product, you don’t have to have much really, and sometimes you’ll need a couple of million dollars to take the next step and reach the next milestone. Sometimes you’ll need less. So yeah it’s fairly broad but early.

Jeffery: But early. Okay, no that’s awesome! Very cool. So we’re looking at now is, through all the time that you’ve been working with early-stage companies, investing, building them, is there a story that really pops in your mind that really shows what it takes to be an entrepreneur? That it could be something where you couldn’t believe that she or he was tackling a problem. They almost failed. They turned it around and boom, they just turned out this amazing business, and it still blows your mind that they were able to do this, and that’s what it takes to be an entrepreneur.

Ash: I’m gonna say there’s a story that just repeats itself. And so, I won’t tell a story of any one person, but just say, sitting on someone’s doorstep until they buy something. When you’re so convinced that what you have is going to be so valuable to them, it is worth just not giving up and showing them that that’s the case. Showing a customer every which way. You’ll meet anyone in their team, you’ll generate any report, you’ll do any analysis, and you’ll do anything for them to come to the realization, that you have that what you do is going to change their business forever. Whether it’s, you know, being able to translate something into 50 languages will help them sell more, or being able to analyze images of their store in real time, or enable them to keep inventory in this store where it’s meant to be kept, or it needs to be kept to turn that inventory over and sell it, or whether it’s, you know, convincing a customer that they can run their kitchen completely differently if they had different software. Just sit there and for those first couple of really big customers, obviously, can’t do this forever because at some point the customers then do this for each other. You know, the old customers do it for the new potential customers but you have to just, and I’ve seen so many great founders just sit there until they realize it, and I really do mean like literally sitting on the doorstep.

Jeffery: I love that. There was an individual that I’ve known for probably 20 years. He’s built many companies. He now heads up Schulich which is one of the top MBA universities in Canada, and that’s one of the things that he talks about all the time, and pushes his guys on sales is that if you believe you’ve got something and that person needs it, –

Ash: Yeah.

Jeffery: – Then don’t stop until that person gets it.

Ash: He’s got it. Yeah. Exactly. Yeah.

Jeffery: He would share stories of finding out where this person was going to be at a bar one night and he would just prop himself up on the bar right beside him.

Ash: Yeah.

Jeffery: Stage it out nicely and then just turn it into a conversation and then turned it into a deal, and he said, “You know, those are the types of things you got to do in order to win the attention of somebody and you can’t let anything –

Ash: Yeah. Exactly, yeah. Yeah, and winning attention is part of it. Like really what you’re trying to do is help them, help them like appreciate the new reality that they need this in order for their business to continue to do well.

Jeffery: And I think that goes down to a comfort level, right? We all are kind of stuck in our own zoned out world, and that when someone’s trying to get in, we gotta treat it like there’s a wall and you gotta climb that wall to get in. You know, at least period and say hi, and then eventually you gotta climb the wall, and jump into their perfume, and start working with them, and those take a lot of time to get them interested.

Ash: Exactly.

Jeffery: No, that’s good. All right, we’re going to jump into our rapid fire questions.

Ash: All right. Let’s do it.

Jeffery: All right. So founder or co-founder?

Ash: Me?

Jeffery: If you were going to, if you’re investing, would you invest in a founder or co-founder?

Ash: Oh, I don’t, I don’t know. I’ve never had that question before.. Founder.

Jeffery: Okay, unicorn or four-year 10 times exit?

Ash: The latter. The former doesn’t mean anything.

Jeffery: I like that. All right, that’s good. Tech or CPG?

Ash: Tech.

Jeffery: Brand or tech?

Ash: Tech.

Jeffery: AI or blockchain?

Ash: AI.

Jeffery: First time founder or second or third time founder?

Ash: Second or third.

Jeffery: First money in or series a?

Ash: First.

Jeffery: Angel or VC?

Ash: VC.

Jeffery: Board seat or observer?

Ash: Board seat.

Jeffery: Safe or convertible note?

Ash: Neither.

Jeffery: Lead or follow?

Ash: Lead.

Jeffery: All right, next question. Do you have any preferred terms that you like to invest on?

Ash: Look, all that really matters is that everyone’s in the same boat on day one. You know, if you’re investing first you’re basically in the same boat as the founder from that point forward you get diluted to the same degree, that’s what really matters. And other than that, you know, it’s just important to respect the money that goes in, as in have terms that protect the investor from being completely wiped out. They’re the most important terms. Now, there are a lot of those terms as protective provisions but they’re extremely important and that’s it. They’re the most important ones.

Jeffery: I like it. What is your favorite part of investing?

Ash: That is really hard. It’s getting to understand lots of different ways to build companies, motivate people, bring different industries, build technologies, whatever, every single day. You know, in a sense what I practice as a craft is the same every single day but where I apply it is different every single day.

Jeffery: I like that. How many investments do you make per year?

Ash: As many as a good, basically. I think the idea of pacing is really absurd, to be honest. Like my job is to be opportunistic and it works both ways when the fantastic opportunities out there, it’s to just not let them pass me by. And when they’re not it’s to not feel like I have to do something. So yeah, I sort of don’t don’t really have an answer to that for that reason. Some years it’s a lot. In some years it’s zero.

Jeffery: Okay, and you do follow on investments?

Ash: Yeah, absolutely. You know, if you’re working with someone and you know about their business and can help them in a unique way, it’s crazy not to.

Jeffery: I love it. Agree. All right, we’re gonna shift into some personal questions and then we’ll clean it up from there. Rapid fire again. Book or movie?

Ash: Book.

Jeffery: Superman or Batman?

Ash: Batman.

Jeffery: Pizza pop or ice cream bar?

Ash: Or both are foreign concepts to me, as an Australian. Last year, I would have said ice cream bar, this year I would say pizza.

Jeffery: All right.

Ash: I have years, years of different preferences.

Jeffery: Yeah. I like it. Five minutes with Bezos or Oprah?

Ash: Bezos.

Jeffery: Yankees or Blue Jays?

Ash: I have no idea. Never followed baseball in my life.

Jeffery: Well, at least you know they’re baseball. So that’s good.

Ash: Yeah, that’s true.

Jeffery: Bike or rollerblades?

Ash: Bikes.

Jeffery: Big mac or chicken mcnuggets?

Ash: I don’t need either.

Jeffery: We gotta pick one.

Ash: No, refuse. Completely refuse. They’re both gross.

Jeffery: It was the only food that I could share that would define between two that people would know what they are because there’s-

Ash: No, no, I honestly just don’t eat either. Yeah, it’s really gross.

Jeffery: It’s still interesting, I guess. Trophy or money?

Ash: Oh, that’s a good one. Money.

Jeffery: Okay, what is your favorite sports team?

Ash: Here’s the funny thing, I’ll play any sport but I just don’t watch any. So it’s hard but I will say AC Milan.

Jeffery: Nice, it’s a good sport. It’s a good team.

Ash: Yeah.

Jeffery: I like it. Okay, favorite movie and what character would you play in the movie?

Ash: That’s a good one. I really like that, maybe Donnie Brasco. It’s fantastic. What character would I play? None of them because I never want to be in the mafia so but I don’t want to be one of the cops in that movie that’s for sure. So I think a lot of my favorite movies are of that ilk. I could also just say, you know, Dr. Noah and James Bond. So yeah, I want to be James Bond. There you go.

Jeffery: Yeah, that’s a good movie. Then, James Bond rocks. So that’s good, too.

Ash: Yeah.

Jeffery: All right, last one. What is your superpower?

Ash: Ah, my superpower is respecting but not being driven by what other people think. I have a second superpower, that’s less mental and more physical which is my heart rate stays very low all the time. So I’m very level and-

Jeffery: Balanced. A nice balance.

Ash: Yeah.

Jeffery: Oh, that’s good. I like it. Well, Ash, I think that today was awesome. I learned a lot

Ash: That was fun.

Jeffery: Somebody else will learn a lot.

Ash: Good ones.

Jeffery: But great job. I’m, again, I’m excited about all the great things that you’re doing. I’m going to keep following you.

Ash: Thank you.

Jeffery: I’m going to write a review on your book because, again, –

Ash: Thank you.

Jeffery: – I thought it was fantastic. I might even help sell your book because I just think that more people need to read and learn about AI because there’s so many misnomers about what it does and the fear of AI is crazy. But great job on all that-

Ash: Thank you.

Jeffery: And thank you again for joining us today. And the way we like to end our show is we like to leave you with the last word. So anything that you want to share to the investor or to the startups, I turn it over to you. But, again, thank you very much.

Ash: Thank you, this is the most generous of you to host me and also continue to help other people understand this field. So, you know, something I’d like to leave people with is, to consider how in making yourself redundant, you empower other people. What can you do every day to make yourself fade a bit more into the background and bring someone else into the foreground?

Jeffery: I like that, brilliant. Very good, very well said.

Ash: Thank you so much. So that was very very fun.

Jeffery: Good, I’m glad you enjoyed it. And again, thank you very much for joining us today Ash. You were fantastic.
Oh, that was awesome. Ash Fontana from building out his book, the lean AI model. You know, it’s just working at zetta. They’re investing in early stage funds, he’s done everything from building out angel lists, just overall fantastic. Really enjoyed the conversation. I think that he brought up a lot of great points and it all comes down to understanding and deploying out how AI works and then diving into supporting, how they support startups, and help them grow and move through the ecosystem. But overall, I just I just loved all of the the details on that so just incredible. So prioritize, address the risk, and the value, know your problem, sell it through, be focused, dive into the company, work with your customers, and make sure you’re solving a problem that they like, and help them understand the problem, and show why you’re going to change their world. Thank you, Ash! Brilliant, all great works! All great works, so thank you for joining us today. If you enjoyed the conversation, please subscribe to our YouTube channel, or follow us on Spotify, Apple Podcast, and/or Stitcher. You can also check us out at supportersfun.com for startup events or visit opn.ninja. Thank you very much guys, have a great day!